Episode 16 | Radiantly Rooted with Rachel
Meet Cheryl Dillon: a certified life coach and connection expert who has spent more than 15 years helping people not just survive, but thrive through major life transitions.
With a background in psychology, professional training from the Institute for Professional Excellence in Coaching (iPEC), and certification in event planning from San Diego State University, she blends emotional insight with thoughtful design to craft experiences that are both uplifting and transformative.
Like many women, Cheryl spent decades doing all the “right” things - working hard, being responsible, and showing up for the people she loves. While she values that deeply, midlife arrived not as a crisis, but as a powerful turning point - a chance to reflect on what she wanted this next chapter to look and feel like.
She realized she didn’t want to buy into the idea that this stage signals a slowdown or that the best years are behind her. Instead, she chose to intentionally design a life rich with depth, joy, and new possibility — and to help other women do the same.
That vision became Funderful Experiences, a company dedicated to helping women shape midlife chapters that feel vibrant, purposeful, and true to who they are. Through her Connected Hearts in-person membership community, The Uplift newsletter, and private coaching, Cheryl brings this mission to life - creating environments that nurture genuine connection, self-trust, and personal growth in ways that feel natural, nourishing, and real.
Her expertise in navigating change is rooted in nearly two decades as co-founder of Equitable Mediation Services, a nationally recognized practice where she has helped people move through divorce with compassion and respect - skills that continue to inform the supportive, judgment-free spaces she creates today.
Cheryl believes midlife isn’t about settling down - it’s the beginning of something truly Funderful.
🔍 What You’ll Take Away from This Episode:
- How Cheryl turned a series of quiet wake-up calls into a bold, joyful midlife reinvention
- Why meaningful experiences matter more than stuff (and how to create more of them)
- The surprising power of puzzles, gardening, and mindful hobbies for getting out of your head
- What it really means to become your own best friend—and how that changes everything
- How to stop the inner critic and build self-trust in your daily life
- What Funderful Experiences is—and why it's changing how women connect, heal, and grow
🌿 Connect with Cheryl Dillon:
Website: https://www.funderfulexperiences.com/
Newsletter, The Uplift: https://www.funderfulexperiences.com/get-the-uplift/
Connected Hearts Membership: https://www.funderfulexperiences.com/connected-hearts-membership/
Instagram: https://www.instagram.com/funderful_experiences/